Holiday houses in Milwaukee County

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Top-rated holiday rentals in Milwaukee County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A cozy living area is highlighted by a light-colored sofa and a circular coffee table at the center. Two windows allow natural light to fill the space, illuminating a decorative rug. A mirror enhances the sense of openness, while potted plants and stylish furniture add softness.
Apartment in Milwaukee
4.98 out of 5 average rating, 105 reviews

Spotless, Walkable- Downtown, Fiserv Forum

Conveniently located in Historic Brewers Hill neighborhood. This upper 2 bed/2 bath unit is centrally located to Fiserv Forum, MSOE. Walkable to Lake Front Brewery and restaurants such as Uncle Wolfies and Avli. Fresh Thyme grocery store is just down the hill. 6 min. walk. We also own a 3 bedroom option. The space hosts up to 7 please visit the link to the lower unit. https://www.airbnb.com/rooms/1609061719132973138guests=1&adults=1&s=67&unique_share_id=f8095770-326a-4972-8fa9-5f8c54574f6b

Guest favourite
Townhouse in Milwaukee
5 out of 5 average rating, 9 reviews

Lux Condo | Garage | Backyard | KING Beds

★Milwaukee's most vibrant neighborhood ★Fenced in backyard ★Free private garage parking ★Free coffee - Free snacks Stay in Milwaukee's most unique suite King George at The Bentley, designed by Peabody's Interiors. Cozy living room, fully equipped kitchen, and two hotel-grade bedrooms set the tone. Spa bath, carrara rain shower, dual vanity, and a wallpapered water closet with a crystal chandelier. King beds, designer bedding, in-unit laundry, private entrance, garage, and a backyard oasis.

Guest favourite
A bright living area showcases a comfortable seating arrangement with decorative cushions. Potted plants add greenery, and light streams in through the large windows. Artwork adorns the walls, while a mix of textures is provided by the rugs and furnishings.
Apartment in Milwaukee
4.94 out of 5 average rating, 442 reviews

Bay View MKE Hideaway - with Parking!

Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

Guest favourite
A spacious back yard overlooks Lake Michigan, featuring a manicured lawn and five comfortable seating options. Sailboats are visible on the water, with a breakwater in the distance. The serene setting is framed by lush greenery, inviting relaxation and enjoyment of the scenic view.
Apartment in Milwaukee
4.86 out of 5 average rating, 316 reviews

Lakeside Beauty

Stunning lower duplex on Lake Michigan in beautiful Bay View WI. Exceptionally large 2 bedroom unit boasts back yard overlooking Lake Michigan with fire pit for cozy evening fires. Unit is a mix of new and classic vintage. Walking distance to South Shore Yacht Club, South Shore Terrace Beer Garden, Award Winning restaurants, a unique European grocery store, and the second largest Farmer's Market in the state. Seven minutes to downtown Milwaukee. Owner lives upstairs. Two bikes available.

Top Guest favourite
A charming upper unit of a bungalow is surrounded by lush green trees and well-maintained landscaping. The exterior features a combination of brick and stone, with decorative patriotic bunting adorning the porch. A pathway leads to the entrance, framed by vibrant foliage.
Apartment in Milwaukee
4.93 out of 5 average rating, 106 reviews

Charming Bungalow Unit Just North of Downtown Milw

Here’s an opportunity that can’t be beat! This fully furnished upper unit in a charming bungalow is ready to be your home base while in Milwaukee. Two bedrooms, one fitted with a king size bed and one with a queen. Full kitchen. Plenty of street parking in this walk able niche neighborhood. Near Downtown, UW-Milwaukee, MSOE, The Milwaukee RiverWalk as well as a quick hop, skip and jump to museums, tours and arenas/stadiums. Easy access to public transportation. No cleaning fees!

Top Guest favourite
A stylish living room features a combination of modern and vintage decor. A leather sofa and two vibrant red chairs are arranged around a wooden coffee table. Decorative plants and unique light fixtures add character, while floral wallpaper and a colorful dining area can be seen in the background.
Home in Milwaukee
5 out of 5 average rating, 168 reviews

Fabulous Walkers Point Mansion w/ Bar andFireplace

This stunning Walker's Point historic mansion is completely re-imagined with interior spaces that will delight you and your guests. Host a memorable get together with friends or family and relax by the bioethanol fireplace, enjoy everything the vibrant neighborhood has to offer. We have some beautiful spaces for your enjoyment, including a finished-attic hangout space, and a secret vintage-inspired lounge in the basement. Enjoy plenty of Milwaukee history in a spectacular new form!

Top Guest favourite
Guest suite in South Milwaukee
4.99 out of 5 average rating, 100 reviews

Historic Hawthorne House

Nestled just steps from Grant Park Beach & Lake Michigan, the scenic Seven Bridges Trail, and the lush Grant Park Golf Course, this unique rental offers a blend of history, charm and comfort. Only a 10 minute drive to Mitchell International Airport and an easy 20 min drive to downtown Milwaukee. Whether you're here to unwind in nature, explore the local parks, enjoy a peaceful lakeside stay, or enjoy the best that Milwaukee has to offer this home has everything you need.

Top Guest favourite
A well-equipped kitchen features white cabinetry, stainless steel appliances, and green tile backsplash. The space is illuminated with recessed lighting and includes a dining area with a wood table. An open doorway leads to another room, enhancing the overall flow of the layout.
Home in Shorewood
4.92 out of 5 average rating, 159 reviews

Shorewood house - near shops w/ WiFi & parking

Just down the road from Lake Michigan, this charming duplex upper is the perfect space for a relaxing getaway. After a day of shopping, eating good food, and exploring Milwaukee, look forward to kicking back in the cozy living room, or on the patio. This duplex has 2 bedrooms; a King bed master, and one bedroom with two Twins. There is one charming bathroom with a bathtub. Well stocked kitchen, and plenty of backyard space. The lower tenant is respectful of guests.

Top Guest favourite
Home in Cudahy
5 out of 5 average rating, 57 reviews

Lake Michigan Views • Private Cedar Sauna

Private cedar barrel sauna, cozy fireplace, and peaceful outdoor spaces just steps from Lake Michigan. Unwind beneath the string lights in the seasonal Garden Lounge, gather around the chiminea, or stroll scenic bluff trails along the lake. Just minutes from downtown Milwaukee, beaches, breweries, restaurants, museums, festivals, and sporting events, this thoughtfully designed getaway is the perfect home base to relax, recharge, and explore year-round

Guest favourite
Home in Milwaukee
4.92 out of 5 average rating, 38 reviews

NEW! Sunny Pet Friendly Upper Unit - Bay View

This sunny upstiars unit of a Bay View bungalow duplex is so sweet and cozy. It features 2 bedrooms, each with a queen bed and closet. The kitchen is stocked with dishes, utensils, pots and pans, microwave, gas range, refrigerator, toaster, and Keurig coffee maker. The bathroom has a shower/bathtub and hair dryer available. Laundry is in the basement and is available for guests to use. Street parking is available, but is not always free.

Top Guest favourite
A spacious bedroom features a white bed adorned with decorative pillows and a textured throw blanket. A striking lion portrait hangs above the bed. Natural light fills the room through a nearby window, with soft curtains partially drawn, complementing the warm brown walls.
Home in Milwaukee
4.95 out of 5 average rating, 255 reviews

Mid-Century Inspired Upper Duplex in Bay View

Step through the carpeted private entrance of this 2nd floor home, and into a mid-century interior with a modern twist. Eye-catching touches include the collection of retro radios that give it its name, stylish decor and a subway-tiled bathroom. This cozy apartment is decorated in a mid-century theme with a modern twist. It's on the second floor of a duplex. You will have your own carpeted entrance located in the back of the property.

Superhost
Apartment in Milwaukee
4.92 out of 5 average rating, 334 reviews

Modern Luxury 1BR Apt with Rooftop+Gym+Parking

Experience Milwaukee like a VIP! This luxury one-bedroom apartment offers the ultimate convenience with direct access to the Fiserv Forum through the building's enclosed skywalk. Whether you're in town for a game, a concert, or simply to explore, you'll love taking in the skyline views from the rooftop patio, working up a sweat in the fitness center, or relaxing in your sleek and comfortable private space.

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